You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:01 UTC
Update Date2019-07-23 06:07:17 UTC
HMDB IDHMDB0030785
Secondary Accession Numbers
  • HMDB30785
Metabolite Identification
Common NameMammeigin
DescriptionMammeigin, also known as 4-chloroquinoline, belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, mammeigin is considered to be a flavonoid lipid molecule. Mammeigin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Mammeigin has been detected, but not quantified in, fruits and mammee apples. This could make mammeigin a potential biomarker for the consumption of these foods.
Structure
Data?1563862037
Synonyms
ValueSource
4-Chloro-quinolineHMDB
4-ChloroquinolineHMDB
5-Hydroxy-6'',6''-dimethyl-6-(3-methylbutyryl)-4-phenylpyrano[2'',3'':7,8]coumarinHMDB
5-Hydroxy-6-isovaleryl-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b,3,4-b']dipyran-2-one, 8ciHMDB
5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ciHMDB
Mammea a/a cyclo DHMDB
Quinoline, 4-chloro- (6ci,7ci,8ci,9ci)HMDB
(5-Hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-phenyl-2H,8H-pyrano(2,3-F)chromen-2-one)MeSH
Chemical FormulaC25H24O5
Average Molecular Weight404.4551
Monoisotopic Molecular Weight404.162373878
IUPAC Name5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-phenyl-2H,8H-pyrano[2,3-f]chromen-2-one
Traditional Namemammeigin
CAS Registry Number2289-11-4
SMILES
CC(C)CC(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O
InChI Identifier
InChI=1S/C25H24O5/c1-14(2)12-18(26)21-22(28)20-17(15-8-6-5-7-9-15)13-19(27)29-23(20)16-10-11-25(3,4)30-24(16)21/h5-11,13-14,28H,12H2,1-4H3
InChI KeyVSDJRZADBKXDHP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassNeoflavonoids
Sub ClassPrenylated neoflavonoids
Direct ParentPrenylated neoflavonoids
Alternative Parents
Substituents
  • Prenylated neoflavonoid
  • Pyranoneoflavonoid
  • 4-phenylcoumarin
  • Pyranocoumarin
  • Angular pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Butyrophenone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 - 145 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP5.24ALOGPS
logP5.45ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.38ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.65 m³·mol⁻¹ChemAxon
Polarizability43.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udm-3209000000-5bc3bdf50677f5476010Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fr6-7212900000-101f4c65041a4fdbc8e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2008900000-21c6869ec172be456110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-4009000000-f17f8af03d1cad413cb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9036000000-efb3917ebbe6b4ae533aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0005900000-8ff8095a713267295b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-2019200000-a562725b55ecdf8973baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ftr-4159000000-8610aeb50115226a3597Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002722
KNApSAcK IDC00010221
Chemspider ID4477593
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319255
PDB IDNot Available
ChEBI ID429835
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Mammeigin → 6-{[8,8-dimethyl-6-(3-methylbutanoyl)-2-oxo-4-phenyl-2H,8H-pyrano[2,3-f]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails